Protopine

Modify Date: 2025-08-21 12:15:40

Protopine structure	Common Name	Protopine
	CAS Number	130-86-9	Molecular Weight	353.369
	Density	1.3±0.1 g/cm3	Boiling Point	547.5±49.0 °C at 760 mmHg
	Molecular Formula	C₂₀H₁₉NO₅	Melting Point	211ºC
	MSDS	Chinese USA	Flash Point	284.9±29.8 °C
	Symbol	GHS06	Signal Word	Danger

Use of Protopine

Protopine, an isoquinoline alkaloid contained in plants in northeast Asia.IC50 Value:Target:In vitro: Protopine was found to reduce nitric oxide (NO), cyclooxygenase-2 (COX-2), and prostaglandin E(2) (PGE(2)) production by LPS-stimulated Raw 264.7 cells, without a cytotoxic effect. Pre-treatment of Raw 264.7 cells with protopine reduced the production of pro-inflammatory cytokines [2]. Protopine is a novel microtubule stabilizer with anticancer activity in HRPC cells through apoptotic pathway by modulating Cdk1 activity and Bcl-2 family of proteins [3]. In HepG2 cells, protopine significantly increased CYP1A1 mRNA levels after 24h exposure at concentrations from 25 and 10 μM. Protopine also dose-dependently increased CYP1A1 and CYP1A2 mRNA levels in human hepatocytes [4].In vivo: Assays were performed on MDA-MB-231 human breast cancer cells, and the result showed that protopine exhibited anti-adhesive and anti-invasion effects in MDA-MB-231 cells; after treatment with protopine for 90 min, the expression of EGFR, ICAM-1, αv-integrin, β1-integrin and β5-integrin were remarkably reduced [1].

Name	protopine
Synonym	More Synonyms

Description	Protopine, an isoquinoline alkaloid contained in plants in northeast Asia.IC50 Value:Target:In vitro: Protopine was found to reduce nitric oxide (NO), cyclooxygenase-2 (COX-2), and prostaglandin E(2) (PGE(2)) production by LPS-stimulated Raw 264.7 cells, without a cytotoxic effect. Pre-treatment of Raw 264.7 cells with protopine reduced the production of pro-inflammatory cytokines [2]. Protopine is a novel microtubule stabilizer with anticancer activity in HRPC cells through apoptotic pathway by modulating Cdk1 activity and Bcl-2 family of proteins [3]. In HepG2 cells, protopine significantly increased CYP1A1 mRNA levels after 24h exposure at concentrations from 25 and 10 μM. Protopine also dose-dependently increased CYP1A1 and CYP1A2 mRNA levels in human hepatocytes [4].In vivo: Assays were performed on MDA-MB-231 human breast cancer cells, and the result showed that protopine exhibited anti-adhesive and anti-invasion effects in MDA-MB-231 cells; after treatment with protopine for 90 min, the expression of EGFR, ICAM-1, αv-integrin, β1-integrin and β5-integrin were remarkably reduced [1].
Related Catalog	Signaling Pathways >> Others >> Others Natural Products >> Alkaloid Research Areas >> Others
References	[1]. Bae DS, et al. Protopine reduces the inflammatory activity of lipopolysaccharide-stimulated murine macrophages. BMB Rep. 2012 Feb;45(2):108-13. [2]. Chen CH, et al. Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines. Cancer Lett. 2012 Feb 1;315(1):1-11. [3]. Vrba J, et al. Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR. Toxicol Lett. 2011 Jun 10;203(2):135-41. [4]. He K, et al. Protopine inhibits heterotypic cell adhesion in MDA-MB-231 cells through down-regulation of multi-adhesive factors. Afr J Tradit Complement Altern Med. 2014 Jan 28;11(2):415-24.

Description

Related Catalog

Signaling Pathways >> Others >> Others

Natural Products >> Alkaloid

Research Areas >> Others

References

[1]. Bae DS, et al. Protopine reduces the inflammatory activity of lipopolysaccharide-stimulated murine macrophages. BMB Rep. 2012 Feb;45(2):108-13.

[2]. Chen CH, et al. Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines. Cancer Lett. 2012 Feb 1;315(1):1-11.

[3]. Vrba J, et al. Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR. Toxicol Lett. 2011 Jun 10;203(2):135-41.

[4]. He K, et al. Protopine inhibits heterotypic cell adhesion in MDA-MB-231 cells through down-regulation of multi-adhesive factors. Afr J Tradit Complement Altern Med. 2014 Jan 28;11(2):415-24.

Density	1.3±0.1 g/cm3
Boiling Point	547.5±49.0 °C at 760 mmHg
Melting Point	211ºC
Molecular Formula	C₂₀H₁₉NO₅
Molecular Weight	353.369
Flash Point	284.9±29.8 °C
Exact Mass	353.126312
PSA	57.23000
LogP	3.76
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.613
InChIKey	GPTFURBXHJWNHR-UHFFFAOYSA-N
SMILES	CN1CCc2cc3c(cc2C(=O)Cc2ccc4c(c2C1)OCO4)OCO3
Storage condition	Refrigerator

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VS2800000

CAS REGISTRY NUMBER :: 130-86-9

LAST UPDATED :: 199803

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C20-H19-N-O5

MOLECULAR WEIGHT :: 353.40

WISWESSER LINE NOTATION :: T I5 F6 C-10-65 DV JO LO PN VO A&O KH&&T&&J P1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. (Washington, DC) Volume(issue)/page/year: 5,24,1953

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 482 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 16(6),7,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 31 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,640,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 237 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 28,767,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 116 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 28,767,1973

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301
Precautionary Statements	P301 + P310 + P330
Safety Phrases	24/25
RIDADR	UN 1544
RTECS	VS2800000
Packaging Group	III
Hazard Class	6.1(b)

Precursor 4
CAS#:64191-02-2 Dihydroprotopine CAS#:6642-34-8 (6-Bromo-1,3-be... CAS#:64603-67-4 5-BROMO-6-(CHLO... CAS#:41431-71-4 cis-N-methylsty...
DownStream 5
CAS#:3486-66-6 Coptisine CAS#:3606-45-9 dihydrosanguinarine CAS#:2447-54-3 SANGUINARINE CAS#:6020-18-4 Coptisine chloride
CAS#:552-29-4 oxyhydrastinine

Name: qHTS for Inhibitors of human tyrosyl-DNA phosphodiesterase 1 (TDP1): qHTS in cells in...
Source: NCGC
Target: TDP1 protein [Homo sapiens]
External Id: TDP1100

Name: qHTS for Inhibitors of human tyrosyl-DNA phosphodiesterase 1 (TDP1): qHTS in cells in...
Source: NCGC
Target: TDP1 protein [Homo sapiens]
External Id: TDP1101

Name: HIV Cellular Data
Source: NIAID
Target: N/A
External Id: HIV Cellular Data

Name: qHTS for inhibitors of Vif-A3G interactions: Validation
Source: NCGC
Target: DNA dC->dU-editing enzyme APOBEC-3G [Homo sapiens]
External Id: VIFG001

Name: Primary Screen Inhibitors of CD40 Signaling in BL2 Cells Measured in Cell-Based Syste...
Source: Broad Institute
Target: N/A
External Id: 7124-01_Inhibitor_SinglePoint_HTS_Activity

Name: Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV)
Source: NCGC
External Id: APP-Toga-CHIKV-nsp2-p

Name: High-throughput screen for inhibitors of the GIV GBA-motif interaction with Galpha-i ...
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
External Id: HMS1303

Name: qHTS for Inhibitors of binding or entry into cells for Marburg Virus
Source: NCGC
Target: gene 4 small orf - Marburg virus
External Id: VSVM-OFFLINE

Name: qHTS for Inhibitors of binding or entry into cells for Lassa Virus
Source: NCGC
Target: N/A
External Id: VSVL-OFFLINE

Name: Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (E...
Source: NCGC
External Id: epac1-activator-v

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Protopin

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BIFLORIN

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Protopine

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